Haloalkenyl alkoxymethyl ether compound and a process for preparing a terminal conjugated alkadien-1-yl acetate compound and a terminal conjugated alkadien-1-ol compound therefrom

Patent metadata

Field	Value
Publication number	US-11560349-B2
Application number	US-202117489905-A
Country	US
Kind code	B2
Filing date	Sep 30, 2021
Priority date	Oct 2, 2020
Publication date	Jan 24, 2023
Grant date	Jan 24, 2023

Abstract

The present invention relates to a haloalkenyl alkoxymethyl ether compound of the following general formula (1): R1CH2OCH2OCH2CH2CH═CH(CH2)aX1 (1) wherein R1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, X1 represents a halogen atom, and “a” represents an integer of 3 to 14. The present invention also relates to processes for preparing a terminal conjugated alkadien-1-yl acetate compound of the following general formula (5): CH2═CHCH═CH(CH2)aOAc (5) wherein “a” is as defined above, and Ac represents an acetyl group, and a terminal conjugated alkadien-1-ol compound of the following general formula (6): CH2═CHCH═CH(CH2)aOH (6) wherein “a” is as defined above, from the haloalkenyl alkoxymethyl ether compound (1).

First claim

The invention claimed is:

1. A process for preparing a terminal conjugated alkadien-1-yl acetate compound of the following general formula (5):
CH 2 ═CHCH═CH(CH 2 ) a OAc  (5)

wherein “a” represents an integer of 3 to 14, and Ac represents an acetyl group, the process comprising:
dealkoxymethylating a haloalkenyl alkoxymethyl ether compound of the following general formula (1):
R 1 CH 2 OCH 2 OCH 2 CH 2 CH═CH(CH 2 ) a X 1   (1)

wherein R 1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, X 1 represents a halogen atom, and “a” is as defined above
to prepare a halo-3-alken-1-ol compound of the following general formula (2):
HOCH 2 CH 2 CH═CH(CH 2 ) a X 1   (2)

wherein X 1 and “a” are as defined above;
acetoxylating the halo-3-alken-1-ol compound (2) to prepare a hydroxyalkenyl acetate compound of the following general formula (3):
HOCH 2 CH 2 CH═CH(CH 2 ) a OAc  (3)

wherein “a” and Ac are as defined above;
halogenating the hydroxyalkenyl acetate compound (3) to prepare a haloalkenyl acetate compound of the following general formula (4):
X 2 CH 2 CH 2 CH═CH(CH 2 ) a OAc  (4)

wherein X 2 represents a halogen atom, and “a” and Ac are as defined above; and
subjecting the haloalkenyl acetate compound (4) to an elimination reaction in the presence of a base to prepare the terminal conjugated alkadien-1-yl acetate compound (5).

2. A process for preparing a terminal conjugated alkadien-1-ol compound of the following general formula (6):
CH 2 ═CHCH═CH(CH 2 ) a OH  (6)

wherein “a” is as defined above,
the process comprising:
the process according to claim 1 for preparing the terminal conjugated alkadien-1-yl acetate compound (5), and
deacetylating the terminal conjugated alkadien-1-yl acetate compound (5) to prepare the terminal conjugated alkadien-1-ol compound (6).

3. The process for preparing the terminal conjugated alkadien-1-ol compound (6) according to claim 2 , wherein the elimination reaction and the deacetylation are carried out in parallel in the presence of a base.

4. A haloalkenyl alkoxymethyl ether compound of the following general formula (1):
R 1 CH 2 OCH 2 OCH 2 CH 2 CH═CH(CH 2 ) a X 1   (1)

wherein R 1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, X 1 represents a halogen atom, and “a” represents an integer of 3 to 14.

5. The haloalkenyl alkoxymethyl ether compound of the following general formula (1) according to claim 4 , wherein “a” represents an integer of 6 to 10.

6. The haloalkenyl alkoxymethyl ether compound of the following general formula (1) according to claim 5 , wherein “a” represents an integer of 6, 7 or 10.

Assignees

• Shinetsu Chemical Co

Inventors

• Miyake Yuki
• Kinsho Takeshi
• Komatsu Ryo

Classifications

• C07C67/287

  by introduction of halogen; by substitution of halogen atoms by other halogen atoms · CPC title

• C07C67/297 Primary

  by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups · CPC title

• C07C67/04

  by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds · CPC title

• C07C29/147

  of carboxylic acids or derivatives thereof · CPC title

• C07C29/132

  by reduction of an oxygen containing functional group · CPC title